#------------------------------------------------------------------------------
#$Date: 2019-11-17 08:56:06 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228972 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/12/7231293.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7231293
loop_
_publ_author_name
'Dharmarwardana, Madushani'
'Arimilli, Bhargav S.'
'Luzuriaga, Michael A.'
'Kwon, Sunah'
'Lee, Hamilton'
'Appuhamillage, Gayan A.'
'McCandless, Gregory T.'
'Smaldone, Ronald A.'
'Gassensmith, Jeremiah J.'
_publ_section_title
;
 The thermo-responsive behavior in molecular crystals of naphthalene
 diimides and their 3D printed thermochromic composites
;
_journal_issue                   39
_journal_name_full               CrystEngComm
_journal_page_first              6054
_journal_paper_doi               10.1039/C8CE00798E
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C42 H46 N2 O6'
_chemical_formula_sum            'C42 H46 N2 O6'
_chemical_formula_weight         674.81
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-07-20 deposited with the CCDC.
2018-08-03 downloaded from the CCDC.
;
_cell_angle_alpha                97.903(9)
_cell_angle_beta                 93.317(9)
_cell_angle_gamma                93.732(8)
_cell_formula_units_Z            1
_cell_length_a                   4.2498(17)
_cell_length_b                   8.217(3)
_cell_length_c                   24.826(7)
_cell_measurement_reflns_used    5983
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.22
_cell_measurement_theta_min      2.49
_cell_volume                     854.9(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXTL Intrinsic Phasing (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type
;
Bruker Kappa D8 Quest CMOS diffractometer (with an Oxford Cryosystems cryostream
cooler)
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'HELIOS optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            21943
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.566
_diffrn_reflns_theta_min         2.491
_diffrn_source                   'I\mS microfocus tube'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (Krause, Herbst-Irmer, Sheldrick, & Stalke;  J. Appl. Cryst. 2015, 48,
3-10)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       fragment
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3953
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0574
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0492P)²+0.2668P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1298
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2460
_reflns_number_total             3953
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce00798e8.cif
_cod_data_source_block           scd1707_OctNDI_T200K_orange
_cod_depositor_comments
'Adding full bibliography for 7231291--7231300.cif.'
_cod_database_code               7231293
_publcif_datablock.id            {83926acc-6b96-4904-97ab-69ab5beb6d78}
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.978
_shelx_estimated_absorpt_t_max   0.997
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
N1 N 0.3243(4) 0.78823(18) 0.11003(6) 0.0223(4) Uani 1 1 d . .
O1 O -0.0553(3) 0.62636(17) 0.05538(5) 0.0309(4) Uani 1 1 d . .
O2 O 0.6264(3) 0.98520(16) 0.16775(5) 0.0295(4) Uani 1 1 d . .
O3 O 0.1321(3) 0.37936(16) 0.26879(5) 0.0287(3) Uani 1 1 d . .
C1 C 0.1533(4) 0.7358(2) 0.05987(7) 0.0227(4) Uani 1 1 d . .
C2 C 0.5209(4) 0.9336(2) 0.12168(7) 0.0225(4) Uani 1 1 d . .
C3 C 0.5967(4) 1.0204(2) 0.07472(7) 0.0207(4) Uani 1 1 d . .
C4 C 0.8070(4) 1.1574(2) 0.08260(7) 0.0237(4) Uani 1 1 d . .
H4 H 0.8967 1.1984 0.1182 0.028 Uiso 1 1 calc R U
C5 C 0.8898(4) 1.2369(2) 0.03832(7) 0.0246(5) Uani 1 1 d . .
H5 H 1.0371 1.3307 0.0440 0.030 Uiso 1 1 calc R U
C6 C 0.7586(4) 1.1797(2) -0.01316(7) 0.0208(4) Uani 1 1 d . .
C7 C 0.5399(4) 1.0407(2) -0.02234(7) 0.0190(4) Uani 1 1 d . .
C8 C 0.2852(4) 0.6841(2) 0.15251(7) 0.0230(4) Uani 1 1 d . .
C9 C 0.4039(4) 0.5313(2) 0.14560(7) 0.0241(4) Uani 1 1 d . .
H9 H 0.5159 0.4983 0.1144 0.029 Uiso 1 1 calc R U
C10 C 0.3613(4) 0.4251(2) 0.18383(7) 0.0235(4) Uani 1 1 d . .
H10 H 0.4429 0.3195 0.1789 0.028 Uiso 1 1 calc R U
C11 C 0.1982(4) 0.4746(2) 0.22946(7) 0.0221(4) Uani 1 1 d . .
C12 C 0.0871(5) 0.6304(2) 0.23657(7) 0.0273(5) Uani 1 1 d . .
H12 H -0.0191 0.6656 0.2683 0.033 Uiso 1 1 calc R U
C13 C 0.1284(5) 0.7350(2) 0.19830(7) 0.0262(5) Uani 1 1 d . .
H13 H 0.0497 0.8412 0.2034 0.031 Uiso 1 1 calc R U
C14 C 0.2632(5) 0.2225(2) 0.26533(8) 0.0287(5) Uani 1 1 d . .
H14A H 0.4963 0.2365 0.2652 0.034 Uiso 1 1 calc R U
H14B H 0.1808 0.1516 0.2313 0.034 Uiso 1 1 calc R U
C15 C 0.1690(5) 0.1443(2) 0.31447(7) 0.0279(5) Uani 1 1 d . .
H15A H 0.2633 0.0369 0.3135 0.033 Uiso 1 1 calc R U
H15B H -0.0637 0.1228 0.3122 0.033 Uiso 1 1 calc R U
C16 C 0.2731(5) 0.2505(2) 0.36837(7) 0.0289(5) Uani 1 1 d . .
H16A H 0.1710 0.3558 0.3699 0.035 Uiso 1 1 calc R U
H16B H 0.5044 0.2764 0.3697 0.035 Uiso 1 1 calc R U
C17 C 0.1942(5) 0.1711(2) 0.41853(7) 0.0290(5) Uani 1 1 d . .
H17A H -0.0367 0.1436 0.4172 0.035 Uiso 1 1 calc R U
H17B H 0.3001 0.0671 0.4177 0.035 Uiso 1 1 calc R U
C18 C 0.2962(5) 0.2821(3) 0.47133(7) 0.0310(5) Uani 1 1 d . .
H18A H 0.1888 0.3856 0.4717 0.037 Uiso 1 1 calc R U
H18B H 0.5263 0.3110 0.4718 0.037 Uiso 1 1 calc R U
C19 C 0.2292(5) 0.2108(3) 0.52329(7) 0.0302(5) Uani 1 1 d . .
H19A H -0.0011 0.1844 0.5238 0.036 Uiso 1 1 calc R U
H19B H 0.3348 0.1069 0.5234 0.036 Uiso 1 1 calc R U
C20 C 0.3431(5) 0.3284(3) 0.57425(8) 0.0350(5) Uani 1 1 d . .
H20A H 0.5727 0.3558 0.5731 0.042 Uiso 1 1 calc R U
H20B H 0.2362 0.4318 0.5739 0.042 Uiso 1 1 calc R U
C21 C 0.2850(6) 0.2629(3) 0.62726(8) 0.0475(6) Uani 1 1 d . .
H21A H 0.0572 0.2428 0.6301 0.071 Uiso 1 1 calc R U
H21B H 0.3733 0.3439 0.6580 0.071 Uiso 1 1 calc R U
H21C H 0.3871 0.1595 0.6279 0.071 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 N1 C1 124.34(15) . .
C2 N1 C8 118.88(15) . .
C1 N1 C8 116.77(15) . .
C11 O3 C14 117.62(14) . .
O1 C1 N1 120.95(16) . .
O1 C1 C6 122.09(17) . 2_675
N1 C1 C6 116.96(16) . 2_675
O2 C2 N1 121.51(16) . .
O2 C2 C3 121.80(17) . .
N1 C2 C3 116.68(16) . .
C4 C3 C7 120.38(16) . 2_675
C4 C3 C2 119.75(17) . .
C7 C3 C2 119.84(17) 2_675 .
C3 C4 C5 120.37(17) . .
C3 C4 H4 119.8 . .
C5 C4 H4 119.8 . .
C6 C5 C4 120.24(17) . .
C6 C5 H5 119.9 . .
C4 C5 H5 119.9 . .
C5 C6 C7 120.61(16) . .
C5 C6 C1 120.08(17) . 2_675
C7 C6 C1 119.31(17) . 2_675
C3 C7 C6 121.61(16) 2_675 .
C3 C7 C7 119.4(2) 2_675 2_675
C6 C7 C7 119.0(2) . 2_675
C9 C8 C13 120.28(17) . .
C9 C8 N1 118.41(15) . .
C13 C8 N1 121.30(17) . .
C8 C9 C10 120.52(17) . .
C8 C9 H9 119.7 . .
C10 C9 H9 119.7 . .
C9 C10 C11 119.36(18) . .
C9 C10 H10 120.3 . .
C11 C10 H10 120.3 . .
O3 C11 C12 115.77(16) . .
O3 C11 C10 124.75(17) . .
C12 C11 C10 119.48(16) . .
C13 C12 C11 120.90(17) . .
C13 C12 H12 119.6 . .
C11 C12 H12 119.6 . .
C12 C13 C8 119.43(18) . .
C12 C13 H13 120.3 . .
C8 C13 H13 120.3 . .
O3 C14 C15 107.65(15) . .
O3 C14 H14A 110.2 . .
C15 C14 H14A 110.2 . .
O3 C14 H14B 110.2 . .
C15 C14 H14B 110.2 . .
H14A C14 H14B 108.5 . .
C14 C15 C16 113.17(16) . .
C14 C15 H15A 108.9 . .
C16 C15 H15A 108.9 . .
C14 C15 H15B 108.9 . .
C16 C15 H15B 108.9 . .
H15A C15 H15B 107.8 . .
C15 C16 C17 114.19(16) . .
C15 C16 H16A 108.7 . .
C17 C16 H16A 108.7 . .
C15 C16 H16B 108.7 . .
C17 C16 H16B 108.7 . .
H16A C16 H16B 107.6 . .
C18 C17 C16 112.52(17) . .
C18 C17 H17A 109.1 . .
C16 C17 H17A 109.1 . .
C18 C17 H17B 109.1 . .
C16 C17 H17B 109.1 . .
H17A C17 H17B 107.8 . .
C17 C18 C19 115.70(17) . .
C17 C18 H18A 108.4 . .
C19 C18 H18A 108.4 . .
C17 C18 H18B 108.4 . .
C19 C18 H18B 108.4 . .
H18A C18 H18B 107.4 . .
C20 C19 C18 112.38(17) . .
C20 C19 H19A 109.1 . .
C18 C19 H19A 109.1 . .
C20 C19 H19B 109.1 . .
C18 C19 H19B 109.1 . .
H19A C19 H19B 107.9 . .
C21 C20 C19 114.60(18) . .
C21 C20 H20A 108.6 . .
C19 C20 H20A 108.6 . .
C21 C20 H20B 108.6 . .
C19 C20 H20B 108.6 . .
H20A C20 H20B 107.6 . .
C20 C21 H21A 109.5 . .
C20 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C20 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C2 1.398(2) .
N1 C1 1.404(2) .
N1 C8 1.456(2) .
O1 C1 1.210(2) .
O2 C2 1.213(2) .
O3 C11 1.363(2) .
O3 C14 1.431(2) .
C1 C6 1.485(2) 2_675
C2 C3 1.488(2) .
C3 C4 1.376(3) .
C3 C7 1.405(3) 2_675
C4 C5 1.404(2) .
C4 H4 0.9500 .
C5 C6 1.372(3) .
C5 H5 0.9500 .
C6 C7 1.410(3) .
C6 C1 1.485(2) 2_675
C7 C3 1.405(3) 2_675
C7 C7 1.418(3) 2_675
C8 C9 1.376(3) .
C8 C13 1.380(2) .
C9 C10 1.386(2) .
C9 H9 0.9500 .
C10 C11 1.389(2) .
C10 H10 0.9500 .
C11 C12 1.385(3) .
C12 C13 1.377(2) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 C15 1.517(2) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.519(3) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.527(2) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 C18 1.514(3) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 C19 1.522(2) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 C20 1.517(3) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 C21 1.516(3) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C2 N1 C1 O1 -166.28(18) . .
C8 N1 C1 O1 12.3(3) . .
C2 N1 C1 C6 13.9(2) . 2_675
C8 N1 C1 C6 -167.48(15) . 2_675
C1 N1 C2 O2 169.07(17) . .
C8 N1 C2 O2 -9.5(3) . .
C1 N1 C2 C3 -11.6(2) . .
C8 N1 C2 C3 169.82(15) . .
O2 C2 C3 C4 4.1(3) . .
N1 C2 C3 C4 -175.26(16) . .
O2 C2 C3 C7 -177.74(17) . 2_675
N1 C2 C3 C7 2.9(3) . 2_675
C7 C3 C4 C5 -0.6(3) 2_675 .
C2 C3 C4 C5 177.61(17) . .
C3 C4 C5 C6 0.8(3) . .
C4 C5 C6 C7 0.0(3) . .
C4 C5 C6 C1 179.98(17) . 2_675
C5 C6 C7 C3 -179.80(17) . 2_675
C1 C6 C7 C3 0.2(3) 2_675 2_675
C5 C6 C7 C7 -0.8(3) . 2_675
C1 C6 C7 C7 179.15(19) 2_675 2_675
C2 N1 C8 C9 -113.0(2) . .
C1 N1 C8 C9 68.3(2) . .
C2 N1 C8 C13 68.2(2) . .
C1 N1 C8 C13 -110.5(2) . .
C13 C8 C9 C10 1.5(3) . .
N1 C8 C9 C10 -177.38(16) . .
C8 C9 C10 C11 -0.2(3) . .
C14 O3 C11 C12 -175.27(17) . .
C14 O3 C11 C10 5.6(3) . .
C9 C10 C11 O3 177.65(17) . .
C9 C10 C11 C12 -1.4(3) . .
O3 C11 C12 C13 -177.33(17) . .
C10 C11 C12 C13 1.8(3) . .
C11 C12 C13 C8 -0.6(3) . .
C9 C8 C13 C12 -1.1(3) . .
N1 C8 C13 C12 177.74(18) . .
C11 O3 C14 C15 177.55(15) . .
O3 C14 C15 C16 -56.9(2) . .
C14 C15 C16 C17 -177.38(17) . .
C15 C16 C17 C18 -178.93(17) . .
C16 C17 C18 C19 -179.29(17) . .
C17 C18 C19 C20 179.08(18) . .
C18 C19 C20 C21 -179.45(18) . .
